4-氨基-N-呋喃-2-甲基苯磺酰胺 | 5626-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氨基-N-呋喃-2-甲基苯磺酰胺
• 中文别名: 4-氨基-N-(2-呋喃甲基)苯磺酰胺；4-氨基-N-呋喃-2-基甲基-苯磺酰胺
• 英文名称: 4-amino-N-(furan-2-ylmethyl)benzenesulfonamide
• 英文别名: sulfanilic acid furfurylamide；Sulfanilsaeure-furfurylamid
• CAS: 5626-92-6
• 化学式: C₁₁H₁₂N₂O₃S
• mdl: MFCD02223638
• 分子量: 252.294
• InChiKey: GDZYTNDTKOAWSN-UHFFFAOYSA-N

物化性质

• 熔点：
  153 °C(Solv: water (7732-18-5))
• 沸点：
  454.5±55.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2935009090

反应信息

• 作为反应物：
  描述：

  4-phenylbenzoyl isothiocyanate 、 4-氨基-N-呋喃-2-甲基苯磺酰胺 以 丙酮 为溶剂， 以0.09 g的产率得到N-((4-(N-(furan-2-ylmethyl)sulfamoyl)phenyl)carbamothioyl)-[1,1'-biphenyl]-4-carboxamide
  参考文献：
  名称：

  Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists

  摘要：

  To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HIS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial beta-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure activity relationships of these compounds were explored. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.050
• 作为产物：
  描述：

  N-(furan-2-ylmethyl)-4-nitrobenzenesulfonamide 在 盐酸 、 tin 作用下， 以 乙醇 、 水 为溶剂， 以100%的产率得到4-氨基-N-呋喃-2-甲基苯磺酰胺
  参考文献：
  名称：

  Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists

  摘要：

  To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HIS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial beta-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure activity relationships of these compounds were explored. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.050

文献信息

• Design and synthesis of leucylaniline derivatives as leucyl-tRNA synthetase inhibitors
  作者：Jinghan Luo、Chengjun Wu、Yanjun Hu、Xingxing Jia、Yu Chen、Tiemin Sun

  DOI：10.1039/d1nj04543a

  日期：——

  By simulating the structure of Leu-AMP, an intermediate of tRNA synthesis, 26 leu-arylamine derivatives were designed and synthesized by retaining leucine and replacing adenosine phosphate with amido-substituted aniline. All compounds were designed under the guidance of computer aided drug design, and their drug-like properties were fully considered. The inhibitory activities of all compounds against

  通过模拟tRNA合成中间体Leu-AMP的结构，设计合成了26个leu-arylamine衍生物，保留亮氨酸，用氨基取代的苯胺代替磷酸腺苷。所有化合物均在计算机辅助药物设计指导下进行设计，并充分考虑了其类药性质。测试了所有化合物对 LeuRS 抑制酶和草分枝杆菌 1180的抑制活性。大多数化合物显示出对 LeuRS 抑制酶和草分枝杆菌 1180的抑制活性。六种化合物（18、19、20、21、24和25 _ _ _ _ _ _) 使用结核分枝杆菌 H37Ra进行筛选。这些化合物对结核分枝杆菌H37Ra有很强的抑制作用。分子对接研究也显示出同样的结果，充分验证了设计思路。我们还发现化合物上氢键受体的存在导致与蛋白质的关键氨基酸形成强氢键。
• Sutani; Shinkawa, Kagaku Kenkyusho Hokoku, 1949, vol. 25, p. 120
  作者：Sutani、Shinkawa

  DOI：——

  日期：——
• Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists
  作者：Sari Yrjölä、Teija Parkkari、Dina Navia-Paldanius、Tuomo Laitinen、Agnieszka A. Kaczor、Tarja Kokkola、Frank Adusei-Mensah、Juha R. Savinainen、Jarmo T. Laitinen、Antti Poso、Amy Alexander、June Penman、Lisa Stott、Marie Anskat、Andrew J. Irving、Tapio J. Nevalainen

  DOI：10.1016/j.ejmech.2015.10.050

  日期：2016.1

  To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HIS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial beta-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure activity relationships of these compounds were explored. (C) 2015 Elsevier Masson SAS. All rights reserved.